RU2012122615A - Новые соединения в качестве модуляторов рецепторов с терапевтическим действием - Google Patents
Новые соединения в качестве модуляторов рецепторов с терапевтическим действием Download PDFInfo
- Publication number
- RU2012122615A RU2012122615A RU2012122615/04A RU2012122615A RU2012122615A RU 2012122615 A RU2012122615 A RU 2012122615A RU 2012122615/04 A RU2012122615/04 A RU 2012122615/04A RU 2012122615 A RU2012122615 A RU 2012122615A RU 2012122615 A RU2012122615 A RU 2012122615A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- carboxylic acid
- azetidine
- benzyl
- phenylpentyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 18
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 106
- 229910052799 carbon Inorganic materials 0.000 claims abstract 64
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 64
- 229910052736 halogen Inorganic materials 0.000 claims abstract 35
- 150000002367 halogens Chemical class 0.000 claims abstract 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 29
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 17
- 125000003118 aryl group Chemical group 0.000 claims abstract 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 10
- -1 diastereomers Chemical class 0.000 claims abstract 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000004677 hydrates Chemical class 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 5
- NTIZEIXVGZTSDA-UHFFFAOYSA-N 1-[[3-chloro-4-(5-phenylpentoxy)-5-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CC=2)=CC(Cl)=C1OCCCCCC1=CC=CC=C1 NTIZEIXVGZTSDA-UHFFFAOYSA-N 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- PYVDURONGSJORP-UHFFFAOYSA-N 1-[[3-(1,3-oxazol-2-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2OC=CN=2)=CC=C1OCCCCCC1=CC=CC=C1 PYVDURONGSJORP-UHFFFAOYSA-N 0.000 claims 3
- PKKFUNYQCGEBMD-UHFFFAOYSA-N 1-[[3-(cyclopenten-1-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2CCCC=2)=CC=C1OCCCCCC1=CC=CC=C1 PKKFUNYQCGEBMD-UHFFFAOYSA-N 0.000 claims 3
- NTLWSXJEEOCEEV-UHFFFAOYSA-N 1-[[3-(furan-2-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2OC=CC=2)=CC=C1OCCCCCC1=CC=CC=C1 NTLWSXJEEOCEEV-UHFFFAOYSA-N 0.000 claims 3
- MCUKDZKTHMVYRP-UHFFFAOYSA-N 1-[[3-(furan-3-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C2=COC=C2)=CC=C1OCCCCCC1=CC=CC=C1 MCUKDZKTHMVYRP-UHFFFAOYSA-N 0.000 claims 3
- DNJLEHRCQIJVLA-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-(1,3-thiazol-2-yl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CN=2)=CC=C1OCCCCCC1=CC=CC=C1 DNJLEHRCQIJVLA-UHFFFAOYSA-N 0.000 claims 3
- JNGHHIHQDZDJPO-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-(1,3-thiazol-4-yl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2N=CSC=2)=CC=C1OCCCCCC1=CC=CC=C1 JNGHHIHQDZDJPO-UHFFFAOYSA-N 0.000 claims 3
- MRBOTJSZKZJGBU-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-(1,3-thiazol-5-yl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=NC=2)=CC=C1OCCCCCC1=CC=CC=C1 MRBOTJSZKZJGBU-UHFFFAOYSA-N 0.000 claims 3
- NKKWNGNPXONYIQ-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-(1h-pyrazol-4-yl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C2=CNN=C2)=CC=C1OCCCCCC1=CC=CC=C1 NKKWNGNPXONYIQ-UHFFFAOYSA-N 0.000 claims 3
- BWFLSLCMQBJCDY-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-(1h-pyrazol-5-yl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2NN=CC=2)=CC=C1OCCCCCC1=CC=CC=C1 BWFLSLCMQBJCDY-UHFFFAOYSA-N 0.000 claims 3
- LIQNDQSCNQWCJD-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-pyrazol-1-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1N2N=CC=C2)=CC=C1OCCCCCC1=CC=CC=C1 LIQNDQSCNQWCJD-UHFFFAOYSA-N 0.000 claims 3
- FBEDLCUMMCCSPW-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CC=2)=CC=C1OCCCCCC1=CC=CC=C1 FBEDLCUMMCCSPW-UHFFFAOYSA-N 0.000 claims 3
- JDYWTXATFDEFLH-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-thiophen-3-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C2=CSC=C2)=CC=C1OCCCCCC1=CC=CC=C1 JDYWTXATFDEFLH-UHFFFAOYSA-N 0.000 claims 3
- KXPHYUDUFCVJPW-UHFFFAOYSA-N 3-[[4-(5-phenylpentoxy)-3-thiophen-2-ylphenyl]methylamino]cyclobutane-1-carboxylic acid Chemical compound C1C(C(=O)O)CC1NCC(C=C1C=2SC=CC=2)=CC=C1OCCCCCC1=CC=CC=C1 KXPHYUDUFCVJPW-UHFFFAOYSA-N 0.000 claims 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 208000027418 Wounds and injury Diseases 0.000 claims 3
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 3
- 230000006378 damage Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 208000014674 injury Diseases 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- PMZXPCVOIJMVII-UHFFFAOYSA-N 1-[[3-(3-methylthiophen-2-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=CSC(C=2C(=CC=C(CN3CC(C3)C(O)=O)C=2)OCCCCCC=2C=CC=CC=2)=C1C PMZXPCVOIJMVII-UHFFFAOYSA-N 0.000 claims 2
- YGGUCDMIRIIOEZ-UHFFFAOYSA-N 1-[[3-(4-methylthiophen-2-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound CC1=CSC(C=2C(=CC=C(CN3CC(C3)C(O)=O)C=2)OCCCCCC=2C=CC=CC=2)=C1 YGGUCDMIRIIOEZ-UHFFFAOYSA-N 0.000 claims 2
- PBWLPRUPGXMMIT-UHFFFAOYSA-N 1-[[3-(5-methylthiophen-2-yl)-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound S1C(C)=CC=C1C1=CC(CN2CC(C2)C(O)=O)=CC=C1OCCCCCC1=CC=CC=C1 PBWLPRUPGXMMIT-UHFFFAOYSA-N 0.000 claims 2
- HTCLWAZZGFNGIL-UHFFFAOYSA-N 1-[[3-(cyclopenten-1-yl)-4-(5-phenylpentylsulfanyl)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2CCCC=2)=CC=C1SCCCCCC1=CC=CC=C1 HTCLWAZZGFNGIL-UHFFFAOYSA-N 0.000 claims 2
- BUVFADUBXTYLBX-UHFFFAOYSA-N 1-[[3-methoxy-4-(5-phenylpentoxy)-5-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C(C=2SC=CC=2)=C(OCCCCCC=2C=CC=CC=2)C(OC)=CC=1CN1CC(C(O)=O)C1 BUVFADUBXTYLBX-UHFFFAOYSA-N 0.000 claims 2
- ZSIXFZCMDCQKLL-UHFFFAOYSA-N 1-[[3-phenyl-4-(5-phenylpentoxy)phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2C=CC=CC=2)=CC=C1OCCCCCC1=CC=CC=C1 ZSIXFZCMDCQKLL-UHFFFAOYSA-N 0.000 claims 2
- NQBLAPKLARDDSP-UHFFFAOYSA-N 1-[[4-(3-methyl-5-phenylpentoxy)-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=CC=CC=1CCC(C)CCOC(C(=C1)C=2SC=CC=2)=CC=C1CN1CC(C(O)=O)C1 NQBLAPKLARDDSP-UHFFFAOYSA-N 0.000 claims 2
- NIGZMWUSILNVMB-UHFFFAOYSA-N 1-[[4-(5-phenylpentoxy)-3-pyridin-4-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2C=CN=CC=2)=CC=C1OCCCCCC1=CC=CC=C1 NIGZMWUSILNVMB-UHFFFAOYSA-N 0.000 claims 2
- QLBUMHRBGSMZFK-UHFFFAOYSA-N 1-[[4-(5-phenylpentylsulfanyl)-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CC=2)=CC=C1SCCCCCC1=CC=CC=C1 QLBUMHRBGSMZFK-UHFFFAOYSA-N 0.000 claims 2
- DGLCALFLMVQQLZ-UHFFFAOYSA-N 1-[[4-(6-phenylhexoxy)-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CC=2)=CC=C1OCCCCCCC1=CC=CC=C1 DGLCALFLMVQQLZ-UHFFFAOYSA-N 0.000 claims 2
- XAXMOKKCZMIYRO-UHFFFAOYSA-N 1-[[4-[2-(4-phenylphenyl)ethoxy]-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CC=2)=CC=C1OCCC1=CC=C(C=2C=CC=CC=2)C=C1 XAXMOKKCZMIYRO-UHFFFAOYSA-N 0.000 claims 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 2
- 208000006820 Arthralgia Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 231100000516 lung damage Toxicity 0.000 claims 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 claims 1
- UALBREDZRPQFER-UHFFFAOYSA-N 1,2-thiazole;1,3-thiazole Chemical compound C=1C=NSC=1.C1=CSC=N1 UALBREDZRPQFER-UHFFFAOYSA-N 0.000 claims 1
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims 1
- UVCRCXLHSIXGGC-UHFFFAOYSA-N 1-[[4-(3-phenylmethoxypropoxy)-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC(C=C1C=2SC=CC=2)=CC=C1OCCCOCC1=CC=CC=C1 UVCRCXLHSIXGGC-UHFFFAOYSA-N 0.000 claims 1
- QFPGBUHFMIKBIN-UHFFFAOYSA-N 1-[[4-[3-[4-(2-methylpropyl)phenyl]propoxy]-3-thiophen-2-ylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1CCCOC(C(=C1)C=2SC=CC=2)=CC=C1CN1CC(C(O)=O)C1 QFPGBUHFMIKBIN-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000010392 Bone Fractures Diseases 0.000 claims 1
- 208000033379 Chorioretinopathy Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000008069 Geographic Atrophy Diseases 0.000 claims 1
- 208000003807 Graves Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010061323 Optic neuropathy Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 201000010183 Papilledema Diseases 0.000 claims 1
- 206010051246 Photodermatosis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010037423 Pulmonary oedema Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 208000019155 Radiation injury Diseases 0.000 claims 1
- 206010063897 Renal ischaemia Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038886 Retinal oedema Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010038926 Retinopathy hypertensive Diseases 0.000 claims 1
- 206010039705 Scleritis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000000491 Tendinopathy Diseases 0.000 claims 1
- 206010043255 Tendonitis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 208000000208 Wet Macular Degeneration Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 210000003423 ankle Anatomy 0.000 claims 1
- 230000003502 anti-nociceptive effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 201000004982 autoimmune uveitis Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 208000011325 dry age related macular degeneration Diseases 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 238000011902 gastrointestinal surgery Methods 0.000 claims 1
- 238000002682 general surgery Methods 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 201000001948 hypertensive retinopathy Diseases 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 208000024765 knee pain Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 208000020911 optic nerve disease Diseases 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- GHCAUEMXBSLMGU-UHFFFAOYSA-N oxadiazole;1,2,5-oxadiazole Chemical compound C=1C=NON=1.C1=CON=N1 GHCAUEMXBSLMGU-UHFFFAOYSA-N 0.000 claims 1
- 230000010412 perfusion Effects 0.000 claims 1
- 230000008845 photoaging Effects 0.000 claims 1
- 230000002028 premature Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000005333 pulmonary edema Diseases 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 210000001525 retina Anatomy 0.000 claims 1
- 201000011195 retinal edema Diseases 0.000 claims 1
- 230000009759 skin aging Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 201000004415 tendinitis Diseases 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 210000000689 upper leg Anatomy 0.000 claims 1
- 230000006453 vascular barrier function Effects 0.000 claims 1
- 210000005166 vasculature Anatomy 0.000 claims 1
- 208000009935 visceral pain Diseases 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- A—HUMAN NECESSITIES
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US26403809P | 2009-11-24 | 2009-11-24 | |
US61/264,038 | 2009-11-24 | ||
PCT/US2010/057336 WO2011066179A1 (fr) | 2009-11-24 | 2010-11-19 | Nouveaux composés comme modulateurs de récepteurs présentant une utilité thérapeutique |
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RU2012122615/04A RU2012122615A (ru) | 2009-11-24 | 2010-11-19 | Новые соединения в качестве модуляторов рецепторов с терапевтическим действием |
RU2012125184/04A RU2012125184A (ru) | 2009-11-24 | 2010-11-19 | Новые соединения в качестве модуляторов рецепторов с терапевтическим действием |
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EP (2) | EP2504323B1 (fr) |
JP (2) | JP2013512243A (fr) |
KR (2) | KR20120098796A (fr) |
CN (2) | CN102712618B (fr) |
AU (2) | AU2010324988B2 (fr) |
BR (2) | BR112012012261A2 (fr) |
CA (2) | CA2780908A1 (fr) |
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IN (2) | IN2012DN05125A (fr) |
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RU (2) | RU2012122615A (fr) |
WO (2) | WO2011066184A1 (fr) |
ZA (2) | ZA201203523B (fr) |
Families Citing this family (12)
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EP2697212B1 (fr) * | 2011-04-14 | 2015-09-09 | Allergan, Inc. | Dérivés de méthylamines bicycliques phényliques en tant que modulateurs des récepteurs de sphingosine-1 phosphate |
CA2865215A1 (fr) * | 2012-02-21 | 2013-08-29 | Allergan, Inc. | Derives de phenoxy-azetidine utilises comme modulateurs des recepteurs de la sphingosine 1-phosphate (s1p) |
US20140171393A1 (en) * | 2012-12-13 | 2014-06-19 | Allergan, Inc. | Novel aromatic thio compounds as receptor modulators |
PL2958913T3 (pl) * | 2013-02-20 | 2019-03-29 | Lg Chem, Ltd. | Agoniści receptora sfingozyno-1-fosforanowego, sposoby ich przygotowania i zawierające je jako środek aktywny farmaceutyczne kompozycje |
WO2014138075A1 (fr) * | 2013-03-07 | 2014-09-12 | Allergan, Inc. | Composés d'acide phosphonique utilisables en tant que modulateurs des récepteurs au sphingosine-1-phosphate |
US20150045328A1 (en) * | 2013-08-08 | 2015-02-12 | Allergan, Inc. | Disubstituted aryl oxy derivatives as sphingosine-1 phosphate receptors modulators |
WO2015021109A1 (fr) * | 2013-08-08 | 2015-02-12 | Allergan, Inc. | Dérivés d'arylazétidine bisubstitués utilisés en tant que modulateurs des récepteurs de sphingosine-1 phosphate |
WO2015073547A1 (fr) * | 2013-11-13 | 2015-05-21 | Allergan, Inc. | Dérivés de phénoxy azétidine disubstitutés utilisés comme modulateurs du récepteur de la sphingosine 1-phosphate (s1p) |
AU2019214265A1 (en) | 2018-02-02 | 2020-07-23 | Astellas Pharma Inc. | Medicine for preventing or treating ophthalmic disease associated with enhanced intraocular neovascularization and/or intraocular vascular permeability |
WO2022220610A1 (fr) * | 2021-04-14 | 2022-10-20 | 주식회사 엘지화학 | Procédé de préparation d'un intermédiaire pour la synthèse d'un agoniste du récepteur de la sphingosine-1-phosphate |
CN117136183A (zh) * | 2021-04-14 | 2023-11-28 | 株式会社Lg化学 | 制备鞘氨醇-1-磷酸酯受体激动剂的新方法 |
KR20220142388A (ko) * | 2021-04-14 | 2022-10-21 | 주식회사 엘지화학 | 스핑고신-1-인산 수용체 효능제의 신규한 제조방법 |
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ZA902794B (en) * | 1989-04-18 | 1991-04-24 | Duphar Int Res | New 3-n substituted carbamoyl-indole derivatives |
US5294722A (en) * | 1992-04-16 | 1994-03-15 | E. R. Squibb & Sons, Inc. | Process for the preparation of imidazoles useful in angiotensin II antagonism |
US5403851A (en) * | 1994-04-05 | 1995-04-04 | Interneuron Pharmaceuticals, Inc. | Substituted tryptamines, phenalkylamines and related compounds |
AU6310198A (en) * | 1997-03-12 | 1998-09-29 | Takara Shuzo Co., Ltd. | Sphingosine analogues |
US6239297B1 (en) * | 1997-09-11 | 2001-05-29 | Takara Shuzo Co., Ltd. | Sphingosine derivatives and medicinal composition |
DE10010067A1 (de) * | 2000-03-02 | 2001-09-06 | Bayer Ag | Neue Imidazotriazinone und ihre Verwendung |
US7074817B2 (en) * | 2001-06-20 | 2006-07-11 | Wyeth | Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
CA2472680A1 (fr) * | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | Antagonistes selectifs du recepteur s1p1/edg1 |
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JP2010502728A (ja) * | 2006-09-07 | 2010-01-28 | アラーガン インコーポレイテッド | スフィンゴシン−1−リン酸(s1p)受容体アゴニスト生物活性を有するヘテロ芳香族化合物 |
AU2007292347A1 (en) * | 2006-09-07 | 2008-03-13 | Allergan, Inc. | Heteroaromatic compounds having sphingosine-1-phosphate (S1P) receptor agonist and/or antagonist biological activity |
WO2008055072A2 (fr) * | 2006-10-27 | 2008-05-08 | Lpath, Inc. | Compositions et procédés pour traiter des maladies et des troubles oculaires |
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